Every year I think about it, the top 3 sort of change.

But my Top 3 mistakes I made as a SaaS CEO:

  • Not constantly hiring, especially for VPs. You need to spend 20% of your time doing this. I hunkered down too much, tried to do too much myself, and let key roles stay vacant for too long.
  • Not “forcing” the team to be more enterprise. I’m not much of a micromanager, but we blew a few key enterprise opportunities because the engineering team didn’t want to do certain things. I should have micromanaged a few key opportunities that were “make or break”, or close to it.
  • Not understanding the playbook, especially after $4m-$5m ARR or so. Not understanding when you become unstoppable. Maybe not finding good enough mentors. This is why I started SaaStr, but in any event, I didn’t understand that SaaS companies that reach $8m+ in ARR, growing 80% or more with net negative churn are basically unstoppable. Now I know 🙂

A bit more here: From Initial Traction to Initial Scale (~$10M in ARR): The Hardest Phase. But — The Cavalry is Coming. | SaaStr

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